Water → 3-[((3S)-3-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidine

HRID 418298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418298
Cl.[CH3:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10].C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:57]1[N:61]2[CH:62]=[CH:63][CH:64]=[N:65][C:60]2=[C:59]([C:66](O)=[O:67])[CH:58]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:2][C@@H:3]1[N:4]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[CH2:5][CH2:6][N:7]([C:66]([C:59]2[CH:58]=[N:57][N:61]3[CH:62]=[CH:63][CH:64]=[N:65][C:60]=23)=[O:67])[CH2:8]1

Komponenten

8

Edukt 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66649356(2S)-2-Methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride

Produkt 1

HCID 591521083-[((3S)-3-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidineAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2S)-2-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine hydrochloride (may be prepared as described in Description 6) (100 mg, 0.270 mmol) in THF (5 ml) was added HOBT.H2O (41.3 mg, 0.270 mmol), HBTU (102 mg, 0.270 mmol) and pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (48.4 mg, 0.297 mmol). The mixture was stirred for 5 minutes before addition of DIPEA (0.118 ml, 0.674 mmol) and the resultant solution stirred at rt for 16 hours. The mixture was then concentrated and the residue partitioned between DCM (10 ml) and water (10 ml), the layers were separated using a hydrophobic frit and the organic layers concentrated to dryness and the crude material dissolved in DMSO and purified by MDAP to give the title compound (85.3 mg) as a white solid.

Aufarbeitung

  1. concentrationThe mixture was then concentrated
  2. customthe residue partitioned between DCM (10 ml) and water (10 ml)
  3. customthe layers were separated
  4. concentrationthe organic layers concentrated to dryness
  5. dissolutionthe crude material dissolved in DMSO
  6. custompurified by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-eb0845f86c284cd9b0afbedca2514b98
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093249B2

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